S-(Methyl-d3) Arylsulfonothioates: A Family of Robust, Shelf-Stable, and Easily Scalable Reagents for Direct Trideuteromethylthiolation

Article Chemistry, Multidisciplinary

Full-Spectrum Fluoromethyl Sulfonation via Modularized Multicomponent Coupling

Kejie Li et al.

Summary: Modular free-assembly construction of mono-, di-, and tri-fluoromethyl sulfones was achieved by combining halides, a sulfur dioxide surrogate, and halofluorocarbons. This method shows great potential and importance in drug discovery.

CCS CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Robust, scalable construction of an electrophilic deuterated methylthiolating reagent: facile access to SCD3-containing scaffolds

Xiao Xiao et al.

Summary: A practical and concise method has been established to obtain a universal deuterated methylthiolating reagent through a one-pot gram-scale operation under mild conditions. This reagent, odorless and electrophilic, has been widely applied to react with various nucleophiles, resulting in valuable SCD3 analogues with excellent deuterium content. Further transformations have been carried out efficiently to obtain significant derivatives with different oxidative states.

CHEMICAL COMMUNICATIONS (2022)

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Review Chemistry, Multidisciplinary

Recent Developments for the Deuterium and Tritium Labeling of Organic Molecules

Sara Kopf et al.

Summary: Organic compounds labeled with hydrogen isotopes are crucial in drug discovery and development in the pharmaceutical industry. Recent advancements have been made in methodologies for isotopic enrichment of organic molecules, including hydrogen isotope exchange reactions, isotopically labeled analogues of organic reagents, and other transformations with isotope incorporation.

CHEMICAL REVIEWS (2022)

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Article Chemistry, Multidisciplinary

Prospects and Challenges in Organosulfur Chemistry

Ming Wang et al.

Summary: This article introduces the importance of sulfur-containing molecules in various fields, as well as sustainable sulfurizing methods and the use of green reagents. It provides insights and applications of organosulfur chemistry transformations for organic chemistry professionals.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2022)

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Article Chemistry, Multidisciplinary

Atom- and step-economic 1,3-thiosulfonylation of activated allenes with thiosulfonates to access vinyl sulfones/sulfides

Xiao Xiao et al.

Summary: A new type of organocatalysis has been developed for the synthesis of highly functionalized vinyl sulfones. The method offers mild conditions, atom- and step-economy, practicability, conciseness, and environmental friendliness. The products can be transformed to vinyl sulfides through isomerization.

CHEMICAL COMMUNICATIONS (2022)

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Article Chemistry, Organic

Palladium-Catalyzed Methylsulfonylation of Alkyl Halides Using Dimethyl Sulfite as SO2 Surrogate and Methyl Source

Yan-Hua Xin et al.

Summary: A novel and efficient method for the synthesis of methyl sulfone derivatives via palladium-catalyzed methylsulfonylation of alkyl halides with dimethyl sulfite has been described. A variety of aryl and alkyl iodides underwent the sulfonylation smoothly to furnish methyl sulfites in moderate to excellent yields.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Materials Science, Multidisciplinary

Protecting Benzylic C-H Bonds by Deuteration Doubles the Operational Lifetime of Deep-Blue Ir-Phenylimidazole Dopants in Phosphorescent OLEDs

Hye Jin Bae et al.

Summary: By deuterating key C-H bonds, the lifetime of blue phosphorescent OLED devices has been increased to 355 hours, with a maximum external quantum efficiency of 25.1% at 1000 cd/m². This method has made a significant contribution to improving the practical performance of OLEDs.

ADVANCED OPTICAL MATERIALS (2021)

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Review Chemistry, Multidisciplinary

The Deuterated Magic Methyl Group: A Guide to Site-Selective Trideuteromethyl Incorporation and Labeling by Using CD3 Reagents

Joost Steverlynck et al.

Summary: The precise installation of a trideuteromethyl group is gaining attention in medicinal chemistry, with potential pharmacological benefits. This review provides an overview of established methods for site-selective trideuteromethylation and discusses the possibility of introducing CD2H and CDH2 groups, serving as a starting point for advancing trideuteromethylation methodologies for synthetic chemists and offering formation strategies for medicinal chemists in drug preparation.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Review Chemistry, Organic

Synthesis, Reactivity and Activation Modes of Fluoroalkyl Thiosulfonates and Selenosulfonates

Clement Ghiazza et al.

Summary: Reagent design plays a crucial role in modern organofluorine chemistry, with a focus on introducing fluoroalkylthio or seleno groups efficiently and selectively. Among them, versatile fluoroalkyl thiosulfonates and selenosulfonates have been at the forefront of recent developments, showing rich chemical reactivity and wide applicability in various studies.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Review Chemistry, Multidisciplinary

Broadening of horizons in the synthesis of CD3-labeled molecules

Qiao Sun et al.

Summary: Efficient methods for the synthesis of deuterated molecules, particularly CD3-containing ones, have been continuously desired in pharmaceuticals and mechanistic understanding. The recent focus has shifted towards direct incorporating CD3 motifs into molecules, along with the development of various approaches. This review provides an overview of preparation methods for CD3-labeled molecules, ranging from conventional functional group interconversion techniques to catalytic approaches, and includes detailed discussions on reaction mechanisms.

CHEMICAL SOCIETY REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Green synthesis of & alpha;-deuterated boronates using DMTT reagent

Zedong Zhang et al.

Summary: An efficient method for the synthesis of deuterated homologation of boronate esters was developed using DMTT as d2-methylene source. The reaction mechanism involves base promoted deprotonation of DMTT to generate d2-sulfurmethylene ylide intermediate, which attacks the boron atom of boronic ester followed by 1,2-migration to afford the deuterated boronic homologues. This provides a unique approach to achieve one-carbon growth under practical mild conditions.

GREEN SYNTHESIS AND CATALYSIS (2021)

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Article Chemistry, Multidisciplinary

Radical-mediated sulfonyl alkynylation, allylation, and cyanation of propellane

Zhen Wu et al.

Summary: This study reveals an efficient and practical method for synthesizing sulfonyl alkynyl/allyl/cyano-substituted BCP derivatives through a novel radical-mediated difunctionalization of propellane, with broad functional group tolerance, high product diversity, gram-scale preparation, and excellent atom-economy.

CHEMICAL COMMUNICATIONS (2021)

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Review Chemistry, Applied